2-Carene in the Prins reaction

Manukov, É. N.; Urbanovich, T. R.; Vyglazov, O. G.; Chuiko, V. A.; Скаковский, Е. Д.

doi:10.1007/bf00598403

Cited by 6 publications

(9 citation statements)

References 6 publications

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“…83 The rearrangement which occurs due to the valence tautomerism makes it possible to obtain functional derivatives of cycloheptatriene. For example, the diene 79 undergoes the Prins reaction to give two hydroxymethylation products, viz., a mono-( 85) and bicyclic one (86). 84 Electrophilic attack on the terminal double bond in compound 79 by a protonated formaldehyde molecule results in homodienyl ion 87, which is stabilised by deprotonation (i) from C(5) to give the alcohol 88, or (ii) from C (10) to give the allylic alcohol 86.…”

Section: Norcaradiene ± Cycloheptatriene Interconversionmentioning

confidence: 99%

Skeletal rearrangements of monoterpenoids of the carane series

Chuiko¹,

Vyglazov²

2003

Russ. Chem. Rev.

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Data on rearrangements of monoterpenoids with the Data on rearrangements of monoterpenoids with the bicyclo[4.1.0]heptane skeleton occurring by ionic, radical and bicyclo[4.1.0]heptane skeleton occurring by ionic, radical and concerted mechanisms are generalised and analysed. The biblio-concerted mechanisms are generalised and analysed. The bibliography includes 135 references graphy includes 135 references. .

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Section: Norcaradiene ± Cycloheptatriene Interconversionmentioning

confidence: 99%

Skeletal rearrangements of monoterpenoids of the carane series

Chuiko¹,

Vyglazov²

2003

Russ. Chem. Rev.

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“…P-Dihydroionol (41 7) affords the theaspiranes (418) and (419) under the same conditions. Reaction of pionone (403) with alcohols in the presence of a one-electron oxidizing agent such as (420) leads to ethers (42 1) as When trans-p-ionol ( 422) is irradiated at 254 nm in ether or in SDDS-H,O media it is converted439 into retro-y-ionol (423). The photochemistry of various dihydroionone derivatives (424) has been described.44n…”

Section: Lonone Derivativesmentioning

confidence: 99%

“…) have been isolated from Aster p r e a l t u ~. ~~~ p-Ionone(403) is transformed by Aspergiffus niger JTS 19 1 into a mixture of derivatives which are useful for flavouringThe same fungus a-ionone (404) into a mixture of products including cis-and trans-3-hydroxy-aionones and 3-0x0-a-ionone.p-Cyclocitral (405) has been ~~n ~e r t e d ~* ~ into the ketone (406) and aldol condensations of citral (30/31) which yield ionone derivatives have been studied under continuous reactor conditions 425. Heating citral (30/3 1) with propanone in the presence of Al,O,-KF gives high yields of a pseudoionone isomer 426.…”

mentioning

confidence: 99%

Monoterpenoids

Grayson¹

1992

Nat. Prod. Rep.

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Introduction 2 2,6-Dimethyloctanes 3 Irregular Monoterpenoids 4 Menthanes 5 Cineol Derivatives 6 Camphanes and Isocamphanes 7 Pinanes 8 Caranes 9 Fenchanes 10 Thujanes 11 Ionone Derivatives 12 Iridanes 13 Cannabinoids I4 References NATURAL PRODUCT REPORTS, 1992-D. H. GRAYSON 533 Table 1 Plant species Abies spp. Abies alba Achillea abrotanoides Ambrosia trcfida A r t em isia scoparia Bidens pilosa Buddleia sal vifolia Cestrum nocturnum Chaerophyllum bulbosum spp. Citrus aurantium var. Citrus limoniu var. Osbeck Comptonia peregrina Cymbopogon distans f. Drucocephalum moldavica Elettaria cardamomum Maton. Elsholtzia blanda E. pilosa E. polysracha E. stauntonii Eucalyptus Pscerta Feronia limonia Fil ipendula ulniar ia Fissistigma shangtzeense Gutierrezia surothrae Hyp t is pee tinu ta H . suaveolens Poit. Hyssopus oficinalis Illicium simonsii Juniperus recurvata var. Levisticum ojicinale Lomatium grayi Melaleuca alternjfolia Melissa oficinalis Mentha arvensis Mercurialis Ieiocarpa Micromeria teneriflae Benth. Momordica charantia Monodoru myristica Murraya spp. M . k wangsiensis Ocimum basilicum 0 lear ia p h logo pap pa Origanum mujorana 0. onites Picea abies Karst. Pinus cretacea Kollenicz. Piper nigrum Ribes nigrum Ribes nigrum Rosa cymosa Salvia lavandulaefolia sspp.

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“…Although it contains a vinylcyclopropane [2,3], 1 has been shown that the two functions are non-conjugated [4][5][6], and they react accordingly, for example, giving products from a Prins reaction in which the cyclopropane remains intact [6].…”

Section: Introductionmentioning

confidence: 99%

Cyclopropyl aziridines: solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

Silverberg

Rabb

Reno

et al. 2014

Heterocyclic Communications

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The N-tosylaziridine 4 of (+)-2-carene 1 was prepared and subjected to solvolytic reactions with weak protic acids. For comparison, the solvolytic reactions of cis-3-carene-N-tosylaziridine 8 were also studied. The solvolyses of 4 were more rapid than those of 8, and both rings were opened in 4, whereas only the aziridine was opened in 8. This leads to the conclusion that the aziridine and cyclopropane rings in 4 can achieve a conjugated transition state.

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2-Carene in the Prins reaction

Cited by 6 publications

References 6 publications

Skeletal rearrangements of monoterpenoids of the carane series

Skeletal rearrangements of monoterpenoids of the carane series

Monoterpenoids

Cyclopropyl aziridines: solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

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